KR20210089158A - 폴리머 네트워크를 형성하는 실란 조성물 - Google Patents
폴리머 네트워크를 형성하는 실란 조성물 Download PDFInfo
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- KR20210089158A KR20210089158A KR1020217013495A KR20217013495A KR20210089158A KR 20210089158 A KR20210089158 A KR 20210089158A KR 1020217013495 A KR1020217013495 A KR 1020217013495A KR 20217013495 A KR20217013495 A KR 20217013495A KR 20210089158 A KR20210089158 A KR 20210089158A
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- South Korea
- Prior art keywords
- carbon atoms
- group
- bis
- silane
- rubber composition
- Prior art date
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 237
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 162
- 229920000642 polymer Polymers 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims description 235
- 229920001971 elastomer Polymers 0.000 claims abstract description 265
- 239000005060 rubber Substances 0.000 claims abstract description 196
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 144
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 72
- 244000043261 Hevea brasiliensis Species 0.000 claims abstract description 58
- 229920003052 natural elastomer Polymers 0.000 claims abstract description 57
- 229920001194 natural rubber Polymers 0.000 claims abstract description 57
- 239000000945 filler Substances 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 36
- 229920002959 polymer blend Polymers 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 223
- 150000001875 compounds Chemical class 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 239000012763 reinforcing filler Substances 0.000 claims description 81
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- 229920005989 resin Polymers 0.000 claims description 69
- 239000011347 resin Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 59
- 125000000524 functional group Chemical group 0.000 claims description 39
- -1 5-triphenoxysilyl- 2- thiapentyl Chemical group 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 229920003180 amino resin Polymers 0.000 claims description 31
- 150000002894 organic compounds Chemical class 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 150000004756 silanes Chemical class 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 16
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 14
- 239000005062 Polybutadiene Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 238000011065 in-situ storage Methods 0.000 claims description 12
- 229920002857 polybutadiene Polymers 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 11
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 9
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 claims description 8
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 claims description 8
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 229920000620 organic polymer Polymers 0.000 claims description 7
- 229920001568 phenolic resin Polymers 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 6
- 229920000459 Nitrile rubber Polymers 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- MQRVFEKCJGCHSY-UHFFFAOYSA-N 1,1,3-tris(propoxymethyl)-3-(3-triethoxysilylpropylsulfanylmethyl)urea Chemical compound C(C)O[Si](CCCSCN(C(=O)N(COCCC)COCCC)COCCC)(OCC)OCC MQRVFEKCJGCHSY-UHFFFAOYSA-N 0.000 claims description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 229910052752 metalloid Inorganic materials 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- MCEKOERWHIKDFW-UHFFFAOYSA-N 1,1,3,3-tetrakis(butoxymethyl)urea Chemical compound CCCCOCN(COCCCC)C(=O)N(COCCCC)COCCCC MCEKOERWHIKDFW-UHFFFAOYSA-N 0.000 claims description 3
- GOKHTAFUTFEUMV-UHFFFAOYSA-N 1,1,3,3-tetrakis(ethoxymethyl)urea Chemical compound CCOCN(COCC)C(=O)N(COCC)COCC GOKHTAFUTFEUMV-UHFFFAOYSA-N 0.000 claims description 3
- GQNTZAWVZSKJKE-UHFFFAOYSA-N 1,1,3,3-tetrakis(methoxymethyl)urea Chemical compound COCN(COC)C(=O)N(COC)COC GQNTZAWVZSKJKE-UHFFFAOYSA-N 0.000 claims description 3
- HYKVLMIRSSYJHF-UHFFFAOYSA-N 1,1,3,3-tetrakis(phenoxymethyl)urea Chemical compound O(C1=CC=CC=C1)CN(C(=O)N(COC1=CC=CC=C1)COC1=CC=CC=C1)COC1=CC=CC=C1 HYKVLMIRSSYJHF-UHFFFAOYSA-N 0.000 claims description 3
- LQPFNWOJRGRPKT-UHFFFAOYSA-N 1,1,3,3-tetrakis(propoxymethyl)urea Chemical compound CCCOCN(COCCC)C(=O)N(COCCC)COCCC LQPFNWOJRGRPKT-UHFFFAOYSA-N 0.000 claims description 3
- DGIHWFDYEFTFBH-UHFFFAOYSA-N 1,1,3-tris(methoxymethyl)-3-(3-trimethoxysilylpropylsulfanylmethyl)urea Chemical group CO[Si](CCCSCN(C(=O)N(COC)COC)COC)(OC)OC DGIHWFDYEFTFBH-UHFFFAOYSA-N 0.000 claims description 3
- PGFRAHKNDUKDSV-UHFFFAOYSA-N 1,1-bis(ethoxymethyl)urea Chemical compound CCOCN(C(N)=O)COCC PGFRAHKNDUKDSV-UHFFFAOYSA-N 0.000 claims description 3
- HTQXIHCFJIPGPV-UHFFFAOYSA-N 1,1-bis(methoxymethyl)urea Chemical compound COCN(C(N)=O)COC HTQXIHCFJIPGPV-UHFFFAOYSA-N 0.000 claims description 3
- VSAWOBIEZVAVJC-UHFFFAOYSA-N 1,1-bis(propoxymethyl)urea Chemical compound CCCOCN(C(N)=O)COCCC VSAWOBIEZVAVJC-UHFFFAOYSA-N 0.000 claims description 3
- DVGSFCGUHUBUNG-UHFFFAOYSA-N 1,3-bis(ethoxymethyl)urea Chemical compound CCOCNC(=O)NCOCC DVGSFCGUHUBUNG-UHFFFAOYSA-N 0.000 claims description 3
- XKALZGSIEJZJCZ-UHFFFAOYSA-N 1,3-bis(methoxymethyl)urea Chemical compound COCNC(=O)NCOC XKALZGSIEJZJCZ-UHFFFAOYSA-N 0.000 claims description 3
- CUPIIXPULXTSDV-UHFFFAOYSA-N 1,3-bis(propoxymethyl)urea Chemical compound CCCOCNC(=O)NCOCCC CUPIIXPULXTSDV-UHFFFAOYSA-N 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 claims description 3
- TWTUCYIMKQSMAA-UHFFFAOYSA-N 2-N,2-N,4-N,4-N,6-N-pentakis(ethoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCOCNC1=NC(N(COCC)COCC)=NC(N(COCC)COCC)=N1 TWTUCYIMKQSMAA-UHFFFAOYSA-N 0.000 claims description 3
- ISCIPQOBDSSQDY-UHFFFAOYSA-N 2-N,2-N,4-N,6-N-tetrakis(ethoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound C(C)OCN(C1=NC(=NC(=N1)NCOCC)NCOCC)COCC ISCIPQOBDSSQDY-UHFFFAOYSA-N 0.000 claims description 3
- UFZBQHSKTVQEMI-UHFFFAOYSA-N 2-N,2-N,4-N,6-N-tetrakis(propoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound C(CC)OCN(C1=NC(=NC(=N1)NCOCCC)NCOCCC)COCCC UFZBQHSKTVQEMI-UHFFFAOYSA-N 0.000 claims description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- PEDRIHRZXCQSBN-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(ethoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCOCN(COCC)C1=NC(N(COCC)COCC)=NC(N(COCC)COCC)=N1 PEDRIHRZXCQSBN-UHFFFAOYSA-N 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 229920002943 EPDM rubber Polymers 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- 239000005010 epoxy-amino resin Substances 0.000 claims description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 229910021485 fumed silica Inorganic materials 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 150000002738 metalloids Chemical class 0.000 claims description 3
- QNNAQMGJWXJRLE-UHFFFAOYSA-N n-(2-aminoethyl)heptanamide Chemical compound CCCCCCC(=O)NCCN QNNAQMGJWXJRLE-UHFFFAOYSA-N 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims description 3
- 239000005056 polyisocyanate Substances 0.000 claims description 3
- 229920000582 polyisocyanurate Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 3
- 239000001587 sorbitan monostearate Substances 0.000 claims description 3
- 229940035048 sorbitan monostearate Drugs 0.000 claims description 3
- 235000011076 sorbitan monostearate Nutrition 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- KKKKKPSGWVVRLJ-UHFFFAOYSA-N 1,1,3-tris(ethoxymethyl)urea Chemical compound CCOCNC(=O)N(COCC)COCC KKKKKPSGWVVRLJ-UHFFFAOYSA-N 0.000 claims description 2
- IVHGQRJQXVQZIL-UHFFFAOYSA-N 1,1,3-tris(methoxymethyl)urea Chemical compound COCNC(=O)N(COC)COC IVHGQRJQXVQZIL-UHFFFAOYSA-N 0.000 claims description 2
- GUXCPWKERAHMQO-UHFFFAOYSA-N 1,1,3-tris(propoxymethyl)urea Chemical compound C(CC)OCN(C(=O)NCOCCC)COCCC GUXCPWKERAHMQO-UHFFFAOYSA-N 0.000 claims description 2
- XDHZQWKEXNRCIW-UHFFFAOYSA-N 1,3-bis(propoxymethyl)-1,3-bis(3-tripropoxysilylpropylsulfanylmethyl)urea Chemical compound C(CC)O[Si](CCCSCN(C(=O)N(COCCC)CSCCC[Si](OCCC)(OCCC)OCCC)COCCC)(OCCC)OCCC XDHZQWKEXNRCIW-UHFFFAOYSA-N 0.000 claims description 2
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims description 2
- BYVIOWWIDPHTQN-UHFFFAOYSA-N 2-N,2-N,4-N,4-N,6-N,6-N-hexakis(phenoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound O(C1=CC=CC=C1)CN(C1=NC(=NC(=N1)N(COC1=CC=CC=C1)COC1=CC=CC=C1)N(COC1=CC=CC=C1)COC1=CC=CC=C1)COC1=CC=CC=C1 BYVIOWWIDPHTQN-UHFFFAOYSA-N 0.000 claims description 2
- RHNKTBQDZZVYBI-UHFFFAOYSA-N 2-N,2-N,4-N,4-N,6-N-pentakis(propoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound C(CC)OCN(C1=NC(=NC(=N1)N(COCCC)COCCC)NCOCCC)COCCC RHNKTBQDZZVYBI-UHFFFAOYSA-N 0.000 claims description 2
- DZPDAGJGKSYURA-UHFFFAOYSA-N 2-N,2-N,4-N,6-N-tetrakis(phenoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound O(C1=CC=CC=C1)CN(C1=NC(=NC(=N1)NCOC1=CC=CC=C1)NCOC1=CC=CC=C1)COC1=CC=CC=C1 DZPDAGJGKSYURA-UHFFFAOYSA-N 0.000 claims description 2
- CPDZRCNACBWVFG-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(propoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCCOCN(COCCC)C1=NC(N(COCCC)COCCC)=NC(N(COCCC)COCCC)=N1 CPDZRCNACBWVFG-UHFFFAOYSA-N 0.000 claims description 2
- FTTVKOCHGICIOC-UHFFFAOYSA-N CO[SiH](CSCN(C(N(COC)COC)=O)CSC[SiH](OC)OC)OC Chemical compound CO[SiH](CSCN(C(N(COC)COC)=O)CSC[SiH](OC)OC)OC FTTVKOCHGICIOC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical group 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 claims description 2
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
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Images
Classifications
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- C07F7/02—Silicon compounds
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- B60C11/00—Tyre tread bands; Tread patterns; Anti-skid inserts
- B60C11/0008—Tyre tread bands; Tread patterns; Anti-skid inserts characterised by the tread rubber
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/203—Solid polymers with solid and/or liquid additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
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- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
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- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/28—Compounds of silicon
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C11/00—Tyre tread bands; Tread patterns; Anti-skid inserts
- B60C11/0008—Tyre tread bands; Tread patterns; Anti-skid inserts characterised by the tread rubber
- B60C2011/0016—Physical properties or dimensions
- B60C2011/0025—Modulus or tan delta
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- C—CHEMISTRY; METALLURGY
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- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- Polymers & Plastics (AREA)
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US201862755619P | 2018-11-05 | 2018-11-05 | |
US62/755,619 | 2018-11-05 | ||
PCT/US2019/059766 WO2020097010A1 (en) | 2018-11-05 | 2019-11-05 | Polymer network forming silane compositions |
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KR20210089158A true KR20210089158A (ko) | 2021-07-15 |
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EP (1) | EP3877459A1 (de) |
JP (1) | JP2022507017A (de) |
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CN (1) | CN113227228B (de) |
BR (1) | BR112021008694A2 (de) |
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US11350694B1 (en) * | 2021-08-27 | 2022-06-07 | Cole Haan Llc | Article of footwear comprising dandelion foam latex materials |
CN116790018A (zh) * | 2022-03-16 | 2023-09-22 | 可汉有限责任公司 | 制造蒲公英乳胶鞋部件的方法 |
WO2024015956A1 (en) * | 2022-07-14 | 2024-01-18 | Sumitomo Chemical Advanced Technologies, Llc, D.B.A. Sumika Electronic Materials | Rubber compositions containing phloroglucinolic resins for use in tire treads of heavy vehicles |
US20240034820A1 (en) * | 2022-07-28 | 2024-02-01 | The Goodyear Tire & Rubber Company | Rubber composition and truck tire |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
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DE4004781A1 (de) | 1990-02-16 | 1991-08-22 | Degussa | Verfahren zur herstellung von mit organosiliciumverbindungen modifizierten fuellstoffen, die so hergestellten fuellstoffe und deren verwendung |
US5268439A (en) | 1991-01-02 | 1993-12-07 | Bridgestone/Firestone, Inc. | Tin containing elastomers and products having reduced hysteresis properties |
FR2673187B1 (fr) | 1991-02-25 | 1994-07-01 | Michelin & Cie | Composition de caoutchouc et enveloppes de pneumatiques a base de ladite composition. |
CA2105719A1 (en) | 1993-06-28 | 1994-12-29 | Rene Jean Zimmer | Silica based aggregates, elastomers reinforced therewith and tire with tread thereof |
US5396940A (en) | 1993-09-17 | 1995-03-14 | The Goodyear Tire & Rubber Company | Sulfur cured rubber composition containing epoxidized natural rubber and silica filler |
US5792805A (en) * | 1995-06-07 | 1998-08-11 | Cytec Technology Corp. | Vulcanizable rubber compositions containing self-condensing alkylated triazine resins having high imino and/or methylol functionality for improved tire cord adhesion and reinforcement |
EP0845016B1 (de) | 1995-08-16 | 2004-07-07 | General Electric Company | Stabile Silanzusammensetzungen auf Silikatträger |
DE69622235T2 (de) | 1995-10-04 | 2003-01-23 | Michelin & Cie | Kautschukmischung basierend auf einem Dienpolymer mit von Organosilanen abgeleiteten Gruppen zur Verwendung in Reifenlaufflächen |
EP0948573B1 (de) | 1996-05-16 | 2006-02-08 | Columbian Chemicals Company | Russ für kraftfahrzeuge und diesen enthaltende kautschukzusammensetzungen |
US6046266A (en) | 1998-09-24 | 2000-04-04 | The Goodyear Tire & Rubber Company | Tire with silica reinforced tread and/or sidewall components |
DE10017654A1 (de) * | 2000-04-08 | 2001-10-18 | Degussa | Organosiliciumverbindungen |
JP5374005B2 (ja) * | 2000-06-16 | 2013-12-25 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | 多官能性ポリオルガノシロキサンをカップリング剤として含むタイヤ用ゴム組成物 |
DE60233661D1 (de) * | 2001-06-28 | 2009-10-22 | Michelin Soc Tech | Kautschukzusammensetzung für reifen, die ein kupplungsmittel der polythiosulfenamid-gruppe enthält |
NZ537861A (en) * | 2002-07-09 | 2008-09-26 | Momentive Performance Mat Inc | Silica-rubber mixtures having improved hardness |
US7138537B2 (en) * | 2003-04-02 | 2006-11-21 | General Electric Company | Coupling agents for mineral-filled elastomer compositions |
US20040214017A1 (en) * | 2003-04-28 | 2004-10-28 | Uhlianuk Peter William | Coatings that contain monomeric and polymeric melamines with attached functional silane groups |
FR2886303B1 (fr) * | 2005-05-26 | 2007-07-20 | Rhodia Chimie Sa | Utilisation d'une combinaison particuliere d'un agent de couplage et d'un agent de recouvrement, comme systeme de couplage(charge blanche-elastomere) dans les compositions de caoutchouc comprenant une charge inorganique |
US7368490B2 (en) * | 2005-11-28 | 2008-05-06 | Momentive Performance Materials Inc. | Rubber compositions comprising unsaturated imidoalkoxysilanes |
US7550524B2 (en) * | 2006-10-06 | 2009-06-23 | Momentive Performance Materials Inc. | Elastomer composition containing mercaptofunctional silane and process for making same |
US10023723B2 (en) * | 2007-06-05 | 2018-07-17 | Momentive Performance Materials Inc. | Process for preparing rubber compositions and articles made therefrom |
EP2070952A1 (de) * | 2007-12-14 | 2009-06-17 | Continental Aktiengesellschaft | Vulkanisierbare Gummimischung und deren Verwendung für Gummiprodukte |
CN102414033A (zh) * | 2009-04-30 | 2012-04-11 | 道康宁公司 | 硅烷改性的弹性体组合物 |
US9267019B2 (en) * | 2011-06-15 | 2016-02-23 | Lion Copolymer Holdings, Llc | Functionalized silica for silica wet masterbatches and styrene butadiene rubber compositions |
JP6328558B2 (ja) * | 2011-10-24 | 2018-05-23 | ブリヂストン アメリカズ タイヤ オペレイションズ エルエルシー | シリカ充填ゴム組成物及びその調整方法 |
GB201121124D0 (en) * | 2011-12-08 | 2012-01-18 | Dow Corning | Hydrolysable silanes |
US10040896B2 (en) * | 2014-09-25 | 2018-08-07 | Hexion, Inc. | Silane functionalized compounds and compositions thereof |
JP2018108936A (ja) * | 2015-05-14 | 2018-07-12 | Jxtgエネルギー株式会社 | シランカップリング剤、シーリング剤組成物、接着剤組成物、ゴム組成物およびタイヤ |
FR3045624A1 (fr) * | 2015-12-17 | 2017-06-23 | Michelin & Cie | Composition de caoutchouc pour pneumatique comportant un agent de couplage azosilane |
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- 2019-11-05 CN CN201980086967.7A patent/CN113227228B/zh active Active
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- 2019-11-05 JP JP2021523469A patent/JP2022507017A/ja active Pending
- 2019-11-05 KR KR1020217013495A patent/KR20210089158A/ko active Search and Examination
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WO2020097010A1 (en) | 2020-05-14 |
MX2021005211A (es) | 2021-07-21 |
CN113227228A (zh) | 2021-08-06 |
US11267955B2 (en) | 2022-03-08 |
BR112021008694A2 (pt) | 2021-08-10 |
US20200140662A1 (en) | 2020-05-07 |
CN113227228B (zh) | 2023-09-05 |
EP3877459A1 (de) | 2021-09-15 |
JP2022507017A (ja) | 2022-01-18 |
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